diff --git a/addons/web_editor/static/lib/jabberwock/jabberwock.css b/addons/web_editor/static/lib/jabberwock/jabberwock.css
index cccaca857f9..5349495296e 100644
--- a/addons/web_editor/static/lib/jabberwock/jabberwock.css
+++ b/addons/web_editor/static/lib/jabberwock/jabberwock.css
@@ -1,78 +1,3 @@
-jw-editor {
-    display: flex;
-    flex-direction: column;
-    position: relative;
-}
-jw-editor {
-    display: flex;
-    flex-direction: column;
-}
-
-.jw-dropdown {
-    display: inline-block;
-}
-.jw-dropdown .dropdown-menu {
-    min-width: 250px;
-    border: 1px solid #000;
-    background-color: #141217;
-}
-
-jw-toolbar input {
-    color: #C6C6C6;
-}
-jw-resizer{
-    display: block;
-    height: 7px;
-    background-color: #eee;
-    border-top: 1px solid #999;
-    text-align: center;
-    width: 100%;
-    line-height: 6px;
-    position: absolute;
-    bottom: 0;
-    cursor: row-resize;
-}
-
-jw-resizer::before {
-    content: "☰";
-    font-size: 6px;
-    margin-top: 1px;
-    display: inline-block;
-    transform: scale(5,1);
-    color: black;
-    vertical-align: middle;
-}
-table.table-picker {
-    position: absolute;
-    background-color: white;
-    border: 1px solid black;
-    -webkit-box-shadow: 2px 2px 5px 0px rgba(0,0,0,.4);
-    -moz-box-shadow: 2px 2px 5px 0px rgba(0,0,0,.4);
-    box-shadow: 2px 2px 5px 0px rgba(0,0,0,.4);
-}
-table.table-picker tr {
-    height: 1em;
-    padding: 0;
-}
-table.table-picker td {
-    width: 1em;
-    border: 1px solid black;
-    padding: 0;
-}
-table.table-picker td.highlight {
-    background-color: #875A7B;
-}
-#jw-device-preview {
-    border-width: 80px 14px 40px;
-    border-radius: 16px;
-    border-style: solid;
-    border-color: #000;
-    background-color: white;
-    width: 400px;
-    height: 700px;
-    margin: auto;
-    display: block;
-}
 ul.checklist > li {
     list-style: none;
     position: relative;
@@ -101,6 +26,28 @@ ul.checklist > li.checked:after {
     transition: opacity .5s;
     opacity: 1;
 }
+
+table.table-picker {
+    position: absolute;
+    background-color: white;
+    border: 1px solid black;
+    -webkit-box-shadow: 2px 2px 5px 0px rgba(0,0,0,.4);
+    -moz-box-shadow: 2px 2px 5px 0px rgba(0,0,0,.4);
+    box-shadow: 2px 2px 5px 0px rgba(0,0,0,.4);
+}
+table.table-picker tr {
+    height: 1em;
+    padding: 0;
+}
+table.table-picker td {
+    width: 1em;
+    border: 1px solid black;
+    padding: 0;
+}
+table.table-picker td.highlight {
+    background-color: #875A7B;
+}
+
 jw-dialog-container {
     position: fixed;
     top: 0;
@@ -145,9 +92,17 @@ jw-dialog-container jw-dialog table.form-table {
 jw-dialog-container jw-dialog table.form-table td {
     border: none;
 }
+
 jw-follow-range {
     position: absolute;
 }
+
+jw-editor {
+    display: flex;
+    flex-direction: column;
+    position: relative;
+}
+
 .jw-fullscreen .jw-fullscreen {
     display: block;
     position: fixed;
@@ -164,6 +119,37 @@ jw-follow-range {
 .jw-fullscreen jw-follow-range {
     z-index: 1;
 }
+
+jw-editor {
+    display: flex;
+    flex-direction: column;
+}
+
+.jw-dropdown {
+    display: inline-block;
+}
+.jw-dropdown .dropdown-menu {
+    min-width: 250px;
+    border: 1px solid #000;
+    background-color: #141217;
+}
+
+jw-toolbar input {
+    color: #C6C6C6;
+}
+
+#jw-device-preview {
+    border-width: 80px 14px 40px;
+    border-radius: 16px;
+    border-style: solid;
+    border-color: #000;
+    background-color: white;
+    width: 400px;
+    height: 700px;
+    margin: auto;
+    display: block;
+}
+
 jw-group[name="templates"] .label {
     width: 90px;
 }
@@ -219,3 +205,26 @@ jw-templates jw-template:hover jw-thumb {
 jw-templates jw-template img {
     width: 100%;
 }
+
+jw-resizer{
+    display: block;
+    height: 7px;
+    background-color: #eee;
+    border-top: 1px solid #999;
+    text-align: center;
+    width: 100%;
+    line-height: 6px;
+    position: absolute;
+    bottom: 0;
+    cursor: row-resize;
+}
+
+jw-resizer::before {
+    content: "☰";
+    font-size: 6px;
+    margin-top: 1px;
+    display: inline-block;
+    transform: scale(5,1);
+    color: black;
+    vertical-align: middle;
+}
diff --git a/addons/web_editor/static/lib/jabberwock/jabberwock.js b/addons/web_editor/static/lib/jabberwock/jabberwock.js
index 630dc005b0a..0f0cdc85648 100644
--- a/addons/web_editor/static/lib/jabberwock/jabberwock.js
+++ b/addons/web_editor/static/lib/jabberwock/jabberwock.js
@@ -7141,7 +7141,7 @@ odoo.define('web_editor.jabberwock', (function(require) {
                 if (parent) {
                     const markers = [];
                     parent.childVNodes.forEach(sibling => {
-                        // Filter and sort the ndoes.
+                        // Filter and sort the nodes.
                         if (setNodes.has(sibling)) {
                             if (sibling.tangible) {
                                 renderingUnits.push(this._createUnit(cache, sibling, rendered));
@@ -8336,12 +8336,42 @@ odoo.define('web_editor.jabberwock', (function(require) {
     function _isAtSegmentBreak(node, side) {
         const siblingSide = side === 'start' ? 'previousSibling' : 'nextSibling';
         const sibling = node && node[siblingSide];
-        const isAgainstAnotherSegment = sibling && _isSegment(sibling);
+        const isAgainstAnotherSegment = _isAgainstAnotherSegment(node, side);
         const isAtEdgeOfOwnSegment = _isBlockEdge(node, side);
         // In the DOM, a space before a BR is rendered but a space after a BR isn't.
         const isBeforeBR = side === 'end' && sibling && nodeName(sibling) === 'BR';
         return (isAgainstAnotherSegment && !isBeforeBR) || isAtEdgeOfOwnSegment;
     }
+    /**
+     * Return true if the given node is just before or just after another segment.
+     * Eg: <div>abc<div>def</div></div> -> abc is before another segment (div).
+     * Eg: <div><a>abc</a>     <div>def</div></div> -> abc is before another segment
+     * (div).
+     *
+     * @param {Node} node
+     * @param {'start'|'end'} side
+     * @returns {boolean}
+     */
+    function _isAgainstAnotherSegment(node, side) {
+        const siblingSide = side === 'start' ? 'previousSibling' : 'nextSibling';
+        const sibling = node && node[siblingSide];
+        if (sibling) {
+            return sibling && _isSegment(sibling);
+        }
+        else {
+            // Look further (eg.: `<div><a>abc</a>     <div>def</div></div>`: the
+            // space should be removed).
+            let ancestor = node;
+            while (ancestor && !ancestor[siblingSide]) {
+                ancestor = ancestor.parentNode;
+            }
+            let cousin = ancestor && !_isSegment(ancestor) && ancestor.nextSibling;
+            while (cousin && isInstanceOf(cousin, Text)) {
+                cousin = cousin.nextSibling;
+            }
+            return cousin && _isSegment(cousin);
+        }
+    }
     /**
      * Return true if the node is a segment according to W3 formatting model.
      *
@@ -17652,6 +17682,7 @@ odoo.define('web_editor.jabberwock', (function(require) {
             const inputType = (cutEvent && 'deleteByCut') ||
                 (dropEvent && 'insertFromDrop') ||
                 (pasteEvent && 'insertFromPaste') ||
+                (key === 'Enter' && (inputEvent === null || inputEvent === void 0 ? void 0 : inputEvent.inputType) === 'insertText' && 'insertLineBreak') ||
                 (inputEvent && inputEvent.inputType);
             // In case of accent inserted from a Mac, check that the char before was
             // one of the special accent temporarily inserted in the DOM (e.g. '^',
@@ -20784,7 +20815,7 @@ odoo.define('web_editor.jabberwock', (function(require) {
                 });
             };
             const openMedia = () => {
-                this.engine.editor.execCommand('openMedia');
+                this.engine.editor.execCommand('openMedia', { media: node });
             };
             const wrapper = {
                 tag: 'DIV',
@@ -21277,7 +21308,7 @@ odoo.define('web_editor.jabberwock', (function(require) {
                 const savedAttach = image.attach;
                 const savedDetach = image.detach;
                 const handleClick = () => {
-                    const params = { image: node };
+                    const params = { media: node };
                     this.engine.editor.execCommand('openMedia', params);
                 };
                 image.attach = (el) => {
@@ -21423,7 +21454,7 @@ odoo.define('web_editor.jabberwock', (function(require) {
                 const fa = domObject.children[1] || domObject.children[0];
                 if ('tag' in fa) {
                     const dbclickCallback = () => {
-                        this.engine.editor.execCommand('openMedia');
+                        this.engine.editor.execCommand('openMedia', { media: node });
                     };
                     const savedAttach = fa.attach;
                     fa.attach = (el) => {